RESUMO
Using 8-aminoquinoline-based aryl carboxamides, the direct ortho-alkylation can be achieved in high yields in the presence of an iron source, 1,2-bis(diphenylphosphino)ethane (dppe) and phenylmagnesium bromide. The reactions proceed without overalkylation and provide high levels of regioselectivity. The benzylation reactions can be performed in air with reagent-grade THF, while the alkylation works well with unactivated secondary bromides and iodides in 2-methyltetrahydrofuran. Moreover, the reactions only require 5-10 min.
Assuntos
Amidas/química , Aminoquinolinas/química , Ferro/química , Alquilação , Brometos/química , Catálise , Furanos/química , Iodetos/química , Compostos Organofosforados/químicaAssuntos
Amidas/química , Ferro/química , Alquilação , Aminoquinolinas/química , Brometos/química , Carbono/química , Catálise , Hidrogênio/químicaRESUMO
A new route to trisubstituted olefins through a palladium-catalyzed alkyne insertion/reduction reaction with unactivated alkyl iodides is reported. The reaction proceeds under mild conditions and tolerates a range of functional groups and substitution patterns. Preliminary mechanistic inquiry suggests that the transformation may proceed through a hybrid radical/organometallic pathway.